


Ugly 'Meet-Cute' & Other Misadventures

by Hans_On



Category: Supernatural
Genre: M/M, Multi
Language: English
Status: In-Progress
Published: 2020-08-27
Updated: 2020-09-07
Packaged: 2021-03-06 22:28:40
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 6,534
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26146417
Author URL: https://archiveofourown.org/users/Hans_On/pseuds/Hans_On
Summary: A collection of Dean and Cas' meeting, getting together, falling in love and general misadventures.(Most chapters are short prompts; specific tags in each chapter)
Relationships: Castiel/Dean Winchester
Comments: 4
Kudos: 14





	1. Drunk B&E

**Author's Note:**

> This is a lovemuppet 'Meet Ugly' prompt. Dean ends up crashing into the wrong apartment and makes an impression on Castiel.

Castiel is in his bedroom, reading over the notes from his last Anthropology class, feeling morose because his field of strength is Linguistics and they have moved on to the substrate of Archaeology - and he has little interest in field work, lack of social skills notwithstanding, he believed indigenous cultures who wished to stay isolated from the modern world should be able to do so without incursion -

When he hears something - or someone, thump violently into his front door.

Castiel sits up in his bed, frozen as he listens before he pulls off his reading glasses and scrambles out of the bed as he hears someone curse and then shout loudly for a ‘Benny’ before he hears the jiggling of his door and then the sound of it opening.

Jesus Christ he hadn’t locked his door!

A brief flash of panic overtakes him and he looks around his bedroom for something to use as a weapon in case this person is angry - they sound loud and argumentative about this ‘Benny’ they are seeking - obviously not him, but he did not want to be caught in any crossfire if he stuck his head out to let whoever know he had the wrong apartment.

He should invest in a baseball bat for his bedroom, Castiel thinks with a dash of wry amusement as the best thing he has in here, ends up being his rather heavy textbook. It’s that or the golden lava lamp at his bedside and he’s rather fond of that, with the tiny bee decals he has stuck on it.

Not that this apartment building was dangerous or anything that would have made him want protection in the past but now apparently there were angry trespassers about.

“Benny!? What-what... the fuck man…” Castiel crept up to the bedroom door and opened it quietly, sticking his head out. Down the corridor he could see a rather tall, well-built guy standing in the middle of his tiny living room, looking around like he was lost. Sandy haired? Dark blonde maybe… chiseled features and in profile a generous mouth.

“Fuuuck… I swear to God…” The guy takes one step toward the left, a staggered sway that makes Castiel’s eyes narrow. He prowls down the corridor, freezes as the guy huffs loudly and then almost dramatically throws himself into Castiel’s easy chair.

He grips his book tightly, easing closer with all the stealth he can manage and then freezes again, horror on his face. His cat Padawan appears from wherever he had been and stalks curiously up to his chair and the closed-eyed intruder in it, sitting himself at the guy’s feet. Castiel is terrified, mind jumping to what could happen to his cat if this guy is a violent drunk - that swaying Castiel’s mind supplied, his B&E was definitely drunk.

Padawan jumps up into the chair, into the guy’s lap and Castiel’s breath catches.

“What the…” The guy is caught as off guard as Castiel and he stiffens in the chair, shooting upright. “Whoa cat… cat? Benny has a - cat?” He raises one hand defensively into the air, leaning back like he’s trying to disappear into the chair and Castiel can’t stand it anymore.

“Hey! Don’t touch him!” He’s still brandishing the tome two-handed - it would be quite a clocking he gave the guy if he hit him but he was too far away - and he tries to look threatening standing in pajama pants and a ratty T-shirt. The guy sitting in his chair is staring at him wide-eyed and Castiel has to focus his attention away from the blinking, confused green eyes checking him over.

“Uhh, who the fuck are you?” The genuinely curious drunk looks down at the cat suddenly kneading his lap to make itself comfortable. “And where’d the cat come from?”

“I have no idea who you are - or who you’re looking for for that matter but I think you have the wrong apartment!” Castiel shouts it almost hysterically and jabs 'Patterns Of Culture' forward. “Push the cat off and get out.”

Torpid blinking meets his demands and the guy looks from Castiel to the cat to the apartment around him back to the Castiel and then his visual trek ends back on the cat, stretching out in the seam of his thighs.

“Huh. This isn’t… Benny’s apartment is it?” Castiel widens his eyes in an incredulous expression that the guy gives a crooked smile to when he looks up again. It softens his face and makes him look unfairly attractive, and Castiel lowers the book unconsciously in response.

“No, wrong… door? Building? I don’t even know.” Why does he feel wrong-footed?! This guy had just broken into his apartment drunk! “Please, just push Pada off your lap and… you know, leave.”

“Dude… I’m so sorry…” The guy scrubs his hands over his face and drags through his hair before looking back at Castiel again. “I must have drank more than I thought I did. You must have been scared out of your head.” His eyes meander down to Castiel’s choice of weapon. “Definitely could have knocked me the fuck out with that. What is that? An Encyclopedia?”

“Uh - it’s… my textbook for Anthropology.” Castiel is standing awkwardly now, posture relaxed and huge book weighty in a one handed grip. He was now casually chatting to the B&E when he should be calling the police, because this guy still looked too comfortable in his chair holding his cat hostage.

Though was Pada the hostage or the guy stuck under him still seemingly trying to not touch said cat. He was wiggling forward in the chair, trying to urge the cat off by moving but all Pada did was shift his body and look back into the man’s face with a demanding reprimand.

“Anthro... huh? Bachelors?” The still unnamed trespasser still seems afraid to touch the cat, arm hovering over it, so Castiel decides to end the awkward stalemate.

“I’m… I’m just going to come get my cat off you.” He puts the book down on the side table next to the love seat and walks up next to the man who looks up at him - and oh, his eyes are green with a burst of hazel and he was gorgeous, Good Lord - and slowly, a heavy, syrupy sort of atmosphere descends as Castiel leans over to pick up Padawan and then retreat slowly.

“Uh, yeah sorry. I - I’m not fond of cats. Scratchy, bitey little overlords.” Castiel almost hugs Padawan to him, as the guy unwinds, relaxes. “Shit… I’m real sorry but my head’s spinning too now. Trust me I - you’re being great… I just need two minutes.” 

And he proceeds to shut his eyes!

Castiel gapes, goes limp with shock and Pada frees himself, jumping from his arms to the relatively close safety of the loveseat. Castiel stands there, fidgety and unsure before he steps back close and - he was not taking advantage! - pushed at the guy’s bicep, a little poking motion.

“Umm...guy? You can’t sleep here.” His voice comes out all strangled and high pitched. 

“Dean.” Gets mumbled back to him. “You?” Castiel shifts from foot to foot. 

“My name is Castiel. Dean? I’ll make you coffee if you want but you can’t sleep here.” He offers as a bribe, hoping the random awkwardness of the gesture might drive him away. Instead, bright green eyes pop open and the guy gives him what can only be called puppy-eyes.

“Would you?” He looks beseechingly to Castiel and toward his little kitchenette. “A cup of coffee would be fucking awesome… Casteel?.”

“Cas-tee-el.” And somehow he ends up, almost by rote, muscle memory, putting on a pot of coffee for his trespasser Dean. He’s behind the counter, looking into the living room at the guy now loose-limbed sprawled in his chair and can’t help his eyes wondering over him.

Maybe he had been hanging out at a bar with friends or something, Castiel thinks, taking in the black, fitted T-shirt, the maroon button down shirt open over it and the stonewashed jeans finished off with combat boots. Maybe he had been at a photoshoot and had too much champagne.

“You from K.U? I honestly can’t place your age… but an Anthropology Bachelor's dude?” Dean’s head lolls and he stares, piercing right across the distance between them. Castiel fidgets, makes himself move pulling out cups - might as well have one too! - and getting sugar and milk as he speaks.

“It’s my Master’s actually. I’m twenty-six and offended. Anthropology isn’t an ‘old-people’ focus, if that’s what you were implying.” He squints, mouth pursed in displeasure as he clicks down the spoons in his hand.

Dean seems to be worried he offended him if the slight grimace is a sign. “No, sorry I meant… well, isn’t it boring? That’s like… studying ancient cultures or something…?”

“Not just ancient ones. We study currently existing cultures as well and the study has many different focuses for that matter. Archaeology, socio-cultural, linguistics - that one is my particular area of focus for my PhD.” Castiel casts his mind for a way to explain it to someone not versed in the faculty. “Think about what we know about ancient cultures and how a lot of it still applies to us today? Not just in language but in things we consider part of civilized society today without realizing - capitalism, trade, governments, class systems…”

“Huh. You’re really passionate about that stuff.” Castiel meets Dean’s gaze and the almost lazy grin on his lips.

“I like it.” He turns away to check on the coffee pot which is finally starting to drip, a nice slow stream of lovely coffee, the scent of cacao filling the air.

“Bet you’re wicked smart. Doing a Masters at twenty-six. I’m turning twenty-four this year…” Dean’s voice goes quiet, trails off. “I’m just a mechanic though. I didn’t even go to college but I was interested in engineering...just stuff didn’t work out…” Castiel looks over his shoulder and Dean looks saddened, his eyes heavy. “My little brother though - as soon as I finished high school I started working ‘cause Sammy’s like… a genius. And I wanted him to be able to go off to school and not have to worry…”

Castiel is stuck like a deer in headlights looking at a veritable stranger pouring his heart out. If this is what bartenders went through, Castiel was now of the opinion they should be paid hourly like therapists. He turns back to the coffee pot, hiding his face.

“You sound like… a good guy Dean. When you’re not crashing into people’s apartments.” Castiel says it lightly and when he turns around he does not look at Dean. “How do you take it?”

A soft, choked sound comes from his easy chair and Castiel flicks his gaze up, curiosity peaked. Dean’s grinning again but it’s a little… edgy and makes him frown.

“I like my coffee black with a little sugar.” Dean enunciates it carefully, pointedly, while Castiel nods and wonders if the alcohol had a resurgence because he does not get the joke. However, he preps two cups - his with a splash of milk - and takes them back into the living area.

Dean makes grabby hands and Castiel hands his cup over, feeling as if he adopted a stray child. Dean is a slurper, he soon shows as he blows and quickly slurps and swallows hot coffee.

“God,” Dean finally slows to breathe, almost panting and Castiel is sure his tongue must be burnt. “Perfect cup of coffee Cas. You’re such a nice morning after - is it morning yet?”

He feels himself flush up to his ears, can hardly believe what he’s hearing. Is this guy flirting with him?

“It’s-it’s just after midnight. And I don’t do morning-afters.” Castiel splutters, flustered and off-keeled.

“No sleep-overs? You? Lies.” Dean’s eyes shine over his cup and Castiel is red-cheeked as he finally sits on the love seat next to a dozing Padawan.

“If someone sleeps over with me then I’m in a relationship. Therefore it’s not a ‘morning after’”. Dean stares after Castiel does his one-handed air quote and then goes into peels of laughter. “What?!” He’s embarrassed and offended and anxious he’s being laughed at until Dean swallows his mirth, expression effervescent.

“I’m sorry… I’m not laughing at you. Plus, that you don’t do morning afters with people is good to know… means your neighbors don’t have to deal with you shuttling… guys and girls out of here huh?”

Castiel damn near spills his coffee on himself sputtering as he stares at the guy fishing for his personal information. Expression still peeled Dean waits as Castiel finally has a taste.

“I date guys who don’t break into my apartment.” He finally says, voice flinty. Dean raises one hand in surrender looking cowed. “But in fairness, I forgot to lock the door…”

“Oh!” And Dean looks shocked, shocked and pleased as Castiel drinks another sip of coffee, blushing and self-satisfied. “Right. Well, I feel very awake now.” With a nervous cough, Dean stands, a pink tinge to his cheeks. “Umm…”

He walks past Castiel and puts his cup down on the side table, next to his Anthro book. Somehow a stub of a pencil fits into the pocket of his snug fitting jeans because he pulls one out and proceeds to scribble something on the first page.

“Right. Yeah.” He looks across at Castiel and rubs at the back of his neck awkwardly. “If, by the way, in the light of day you don’t want to actually talk to a drunk mechanic who wandered into your home… I mean, I’d completely understand. But if, y’know…”

They become locked in some staring battle of wills and Dean is who breaks, eyes downcast as he blushes.

“Call me.” 

In the morning, bright and early at seven, Castiel messages the number left in his book.

_07:02[Unknown] - Good morning Dean._  
_07:03[Unknown] - I prefer to text._


	2. Sunday Walk Of Shame

**Summary for the Chapter:**

> Another lovemuppet prompt, Dean and Cas meet when they're both doing the morning after ritual.

  
“I’m such a spaz, totally forgot…” Dean is rambling and using every excuse as he grabs his shirt, keys, jumps and wriggles into last night’s jeans from… (Kelly? Carrie? Shelly!) Shelly’s floor. 

“Do you have to go right now?’ The big blue eyes look hurt as Shelly ties her flimsy negligee robe and gestures at what she’s doing in the kitchenette of her apartment. “I was making us breakfast?”

“I’m sooo sorry but I’m going to be in trouble if I’m late.” He pats himself down for his wallet and phone in his jeans, check. He pulls his shirt over his head and spots his jacket on the back of the couch they had stumbled in past last night. His eyes light up, final item!

Dean snatches it and with a final mental rundown, looks at the lovely fitness instructor he had met last night, turning up his expression to ‘maximum apology’. “Last night was lovely.”

It was, had been, good. Not groundbreaking but good. He liked leaving on that note and an awkward morning after meal together when he saw this going nowhere was not the way to do that. So Dean opens her apartment door and steps out into the hallway before swiveling and shaking his head again.

“I spend my afternoons with my mom and kid brother usually on Sunday and I’ve got my own place so chores and stuff - I’d stay a little bit if I could but then my niece…” May God not strike him down for bringing little Maddy into his strategic retreat. “My niece…”

Dean gets distracted by another door down the hallway opening and a guy almost stumbling his way out. He’s got on a buttoned-down, charcoal gray dress shirt and black slacks with a bright blue tie like he came from something formal - but that sex hair says ‘booty call’. He doesn’t even seem to notice anyone else around him as he turns around and ‘oops’, Dean stares, ‘nother dude enters the doorway. 

Other dude was standing in the doorway, almost blocking it with his body and an arm as earnest-looking tanned dude started to stutter out his plea.

“... wouldn’t mind going out with you again - umm, if you want to call me -” Whoever deep-voiced guy is down the hall with his coat rolled up in his hand and his tie hanging crooked off him, he’s dead out of luck. The guy shoots him down quickly and closes the door and Dean gets back to his own self-extraction.

“-yeah, so I’m really sorry but you know, my kid brother’s daughter’s birthday is today too so I gotta go but I have your number. I’ll totally call you.” Dean gives his best winning grin as he finally hops into his other boot and the blonde frowns at him, reading through his bullshit.

“...you know what? Sure. Enjoy your niece's birthday party.” Sadness turns to disappointed irritation in an instant and Dean winces as the door is slammed in his face.

Dean gives a shake of his head at the door with a tiny huff at himself, shrugs into his jacket and then his eyes just get pulled up to the dejected looking guy coming toward him. They both have to go the same way to get out of the apartment building and Dean wonders if he’s taking the elevator or the stairs.

“Hey,” He only knew the guy was dejected really by the slightest curve in of his shoulders and because he saw what happened before. Looking into his face though at Dean’s greeting, he is composed, gaze measured and steady as he turns his face up slightly. Dean’s next inhale is sharp at the brilliant blue of this guy’s eyes, a shade so different from the woman he had just left and frankly stunning. He’s never seen anyone with that intense of an eye color before.

“Hello.” The stranger returns, voice rough and quiet. He looks away, eyes pulled back down to focusing on the ground before his feet and Dean finds himself kind of falling in step as they both go for the stairs.

“Rough night huh? Saturdays…” Dean kind of trots down the stairs while the guy walks confidently, purposefully next to him. He finds himself pausing on landings because he wants the guy to keep up.

The guy’s brows furrow, his lips pursing and Dean’s magnetized, his eyes get drawn there too and Dean’s marking all these new things about this guy that are attractive, reeled in. He’s got a cleft in his chin Dean would worship with his teeth.

“I wouldn’t know.” Oh, his voice was still gravel low, growly and Dean had thought he’d been choked up when he said ‘hello’ but apparently that was this guy’s voice. “I don’t… make a habit of sleeping out with people on my Saturday night.” Ouch, Dean physically leans back from the assumption, offense quickly rising. The guy tucks his head in and walks past him, his coat clenched in his hand and Dean feels for him suddenly.

Shelly had been someone he just met at a bar and went home with. If this guy didn’t do pick ups that meant he had ended up in bed with someone he probably liked and just been dropped like a sack of potatoes after being used.

“That’s fair. I might do the occasional pick-up on my Saturdays here and there but how I meet people, what I do… I think we’re both aware it’s casual.” He pitches it to the guy’s back, swallowing his pride and accepting the jab but clarifying it in the face of this dude’s self-righteous judgement. “Someone may hope it can lead to something more permanent but that’s not what they signed up for.” Dean picked up, but they knew it was meant to be a pick-up. If he saw something he liked he turned the charm up to ten, if they were game, sweet. If not, their loss and Dean moved on.

The guy pauses, and Dean slows as he catches up before the guy moves again. Second floor landing, one more flight and they would part ways, Dean thinks as they move, him two stairs behind the dude.

“We went out to dinner. Ini - he, is someone I work with and I thought we…” When the guy rakes his hand through his hair and tugs at it, he sends it into even more disarray with an adorable tuff sticking out at the front. “It is perhaps my fault for assuming it was more than just a date and casual sex. It’s not like he said he wanted to date me.”

“I’m sorry man. That’s rough if you liked him… and now you still have to work with him.” The cynical chuckle that gets makes Dean wince, the coldness gives him an idea of what Mr. Workmate was going to be subjected to. “You can think what you want about casual sex but the way I do it, I don’t go breaking people’s hearts. I don’t doubt that guy at least had an idea you liked him.”

“So what? Casual sex is safer? Better?” Gravel-rumble voice fires back and Dean realizes as he hits the last step that they’re in the lobby, walls lined with people’s post boxes and the lobby is a length of less than ten feet out the front doors and into the wide world without this guy’s company.

He gives a shrug of one shoulder. “If all you want is company and to feel close to someone without expectations for more than you can give then...yeah.” Deans responds bluntly, without the slightest hint of shame. “I’m Dean by the way.” He sticks his hand out.

He looks at Dean’s hand, brows drawing together cutely as he looks confused. When he looks up he tilts his head at Dean who just arches an eyebrow and waits.

“Castiel.” Finally his hand is taken and shook. Bed-head sex voice has a name and boy!

“That’s a name. Nice to meet you.” Dean laughs, lingering in the squeeze of warm fingers before they disengage.

“I like it.” Castiel says dryly, almost sardonic. He’s probably heard it all about his name. Dean shakes his head, grin going crooked, sly.

“I like it too.” Dean ends up digging for his wallet, digging into a back pocket of his jeans with difficulty. “So - not that you have to necessarily subscribe to my thinking but,” He pulls out one of his business cards and hands it over jauntily between two fingers. “If there’s a Saturday you feel you might want to grab a drink or watch a movie… with a guaranteed happy ending, you can call me.” He can’t help the wink, dies inside a tiny bit in embarrassment but Castiel takes the card almost automatically, eyes glued to it.

“Thank you?” The 'you' pitches up and Dean fights a blush as the guy looks back up at him searchingly, even more confused the longer he stares.

“You should be. I don’t give out my card to just anybody.” He’s definitely never done it to try to pick someone up or flirt before, seeing as all his work stuff is on it along with his cell number. “But, I think I can trust you to not be a stalker type.” Dean hazards the joke grinning as the guy squints suspiciously before rolling his eyes.

“Goodbye Dean.” The dry tone and irritated but reluctantly amused expression has Dean opening the door for the guy and Castiel brushes past with one last look before going on his way as Dean steps out behind him. 

He squints up into the bright daylight, shrugging off the guilt that he probably just threw a business card into the wind as the things weren’t freaking cheap but sucks it up and focuses instead on where he can get wrapping paper for Maddy’s birthday.

**Notes for the Chapter:**

> Comments welcomed, kudos loved! <3


	3. Doggone Shirtless on Benches

**Summary for the Chapter:**

> Dean is working out when he suddenly finds himself with a dog in his shirt. How that leads to a date only Chuck knows.

**Notes for the Chapter:**

> So continuing the Meet Cute prompts, 'Dean is at the park working out while his dog is in the run when Castiel’s dog ends up in his shirt and Castiel has to help get him out' (Lily) + 'Castiel wants to meet the artist behind the beautiful craftsmanship of the bench in the dog park gazebo… turns out it’s Dean!' (KhajitTink) 
> 
> My wonderful beta for this one is evie2268 - thank you! <3

Zepp is inside on the run with some other dogs, dashing back and forth like a madman with his friends. Dean recognizes a Labrador, who is rolling around with a Yorkie, as Ms. Perkins' dog, a heavily-panting Great Dane as belonging to one of his neighbors, and Jo’s Golden Retriever roughhousing with him.

Zepp is a tan and black blur, the German Shepherd dashing back and forth, burning off energy inside the enclosed area. Dean can tell he needs some time to tire himself out and calm down after all the playing, so he finds something to do.

He wanders away to a less congested area of the dog park, halfway down the path to a gazebo but where he can keep an eye on Zepp. He sits on the grass, might as well work out now that he has time to kill.

He goes through bicycle crunches, sit-ups, mountain climbers and puts himself in the plank position for some plank dips when he feels something weird rubbing against his stomach and looks down to suddenly find that his shirt is being stretched out by a Corgi.

Dean splutters, at the first press of a wet nose into his chest and then the wiggle of fur against him. He finds the little brown and black head coming out of the neck of his T-shirt. It all happens so fast, but it seems the little guy got stuck in his shirt collar. Dean brings his knees down and hears someone shouting.

“Oh my God, Cordon!” He turns his head from where he is still knelt in the grass, hunched over a stranger's dog, and assumes this is the owner. A trim guy in running shorts and a sleeveless shirt is jogging up, face flushed from embarrassment as he sees Dean’s situation. His voice is a gravelly rasp that Dean does not think fits the package. “I’m so, so, so sorry! He was running with me, and he gets excited and-”

“It's fine. I’m fine, just trapped.” Dean cuts off his rambling with a smile, looking back down and getting a face full of grinning canine. “You look satisfied with yourself though.”

He looks back up at the dark-haired guy, who kneels hesitantly next to him and sits back on his heels. 

“Just hold onto his stomach, and I’ll get him out.” Dean offers as the stranger's hands hover near his torso, obviously uncomfortable with the idea of touching someone he just met. The guy blushes adorably and holds his dog by the hips, steadying the wriggling puppy and managing to only brush Dean’s damp skin once.

With Cordon finally somewhat secured, Dean reaches for the back of his shirt over his shoulders and pulls it forward over his head, and the dog’s, and suddenly they’re both free. Immediately the dog is a squirming mass in his owner’s hands, but he grabs him more firmly and hugs the dog to his chest, wide-eyed as Dean finally gets to lean back, taking a breath.

“Whoo. Well, this is the first time I’ve ever gotten shirtless for a dog.” Dean gives the guy a grin and laughs as the blush comes back even redder than before, a tan hand running over his face.

“Again, seriously...I’m so sorry. Cordon is very excitable, but he usually stays with me while we run. He just veered off and barrelled straight for you while you were exercising, and I couldn’t catch him…” Cordon visibly tries to make a run for it again, and Dean realizes he still doesn’t know the guy’s name. When the dude gives him a distressed look with the cutest smile, Dean does a mental double-take. “Can you hold him for me, please? His leash is in my pocket.”

Pocket? Dean tries to make it not look obvious that he is searching for a seemingly invisible pocket. He takes the dog and holds him firmly, getting a snout in his face for his trouble while the guy unsnaps a small pocket, pouch really, on his pants and Dean tries not to stare and marvel at the runner’s thighs. Nylon twisted rope in a figure eight-esque loop is revealed and the dog is swiftly hooked and captive at last.

The moment Dean puts him down, the Corgi is back on him practically in his lap, sniffing all over his neck and face, paws on his chest.

“Oh gosh. Cordon, heel.” Surprisingly, for him at least, the dog obeys, going to lie by his owner’s thigh. “He’s incorrigible.”

“I’m used to being a chick magnet but apparently I attract males too.” Dean winks, smirking as the guy looks away flustered. Nice, even nicer when he catches the man sneaking a peek at Dean as he turns his shirt out the right way before pulling it back on. “My dog Zepp is running around, the hyper German over there,” Dean points and takes the chance to give the guy a quick once over. He is cute: dark hair, blue eyes, and muscularly full-bodied. It wasn’t like he was dating anyone right now…so why not. “If you want to keep walking with your dog I can join you, I just need to let my friend know to keep an eye on Zepp for me.”

“Oh,” Shock followed by a pleased smile is the response to his offer, so Dean stands and offers a hand. The guy’s grip is firm and hauling him up is easy as the dude pulls his own weight. He was ticking all of Dean’s boxes. “Yes, that- I’d love it if you joined me.”

It’s nothing but a quick jog over to Jo to let her know he’s going on the walking path and then a leisurely stroll back over to where the cutie is standing with his dog. It’s funny, both of them are like awkward teens making indirect eye contact as he walks back, but he takes the opportunity to check him out again, more thoroughly, and Dean has to admit that he’s attracted.

“I have just realized that we are forgetting a really big part on this walk um, talking?” The man switches the leash to his left and holds out his now free dominant hand. “I’m Castiel. Castiel Milton, and it’s a pleasure to meet you.”

“Dean Winchester and the pleasure is all mine.” He really doesn’t mean it to come out like a flirt but it does, his voice low and intimate, so he rolls with it. “I’m bi by the way, you?”

Castiel huffs out a surprised laugh at the new information that was offered and his reply comes out on a breathy chuckle. “Gay. Both definitions.” Dean considers his risk rewarded if Castiel is happy and has to fight to control his laughter as Cas' is infectious.

They grin at each other and after Dean makes an ‘after you’ gesture, they start walking again.

The walker’s path winds through the park, circling the gazebo in the center of the place. They meander toward it, with Cordon now at a happy trot between their feet. Dean is pleased that he’s more controlled on his leash, especially so Castiel can focus on him.

“Do you usually work out at the dog park? I’m sure I would have noticed you before.” He angles a look towards Castiel who he catches staring back at him before his blue eyes skitter away. Dean’s genuinely flattered by the subtle compliment because while he’s been told he’s good looking, he gets the feeling Castiel isn’t usually this brazen.

“Hmm no, I don’t usually work out here, but I bring my dog to run and play often. He’s familiar with the park and a lot of the dogs that come in around this time. I come here pretty regularly; I’m just not usually on the lawn where Cordon found me.” Dean offers, keeping his gaze on Castiel’s face as he exhales an ‘ah’ of understanding.

“I’m here twice every day. I come during the mornings and find myself back here later in the evenings as well. The only reason I’m earlier than usual today is because Park Services closes at four-thirty, and I wanted to ask a question about something.” Castiel gives a small chuckle that Dean immediately finds himself yearning to hear again. Dean flushes at his thoughts and is eternally grateful when Cas makes another comment seemingly unaware of his colored cheeks. “I’m very glad I decided to come now though…”

“I’m glad your dog is into planks.” Dean returns wittily and then almost stumbles over his own feet in delight at seeing the full-blown laughter that bursts from Castiel, revealing an adorably open smile under squinted, shining eyes. He’s sold, he’s super sold. “Hopefully you’re into them too; I’d love to get your number. We could go out and chat somewhere, that’s not a dog park.”

“Yeah, of course. I’d…” Castiel’s flushed face is gorgeous and Dean is sending up a prayer that this could be the start of something and feeling a twist of excitement in his stomach he hasn’t felt in a while. “Umm, I don’t have my phone on me but if you do I can give you my number.”

They’re almost to the gazebo so Dean tilts his head there, pulling them off the path. “Yeah, I do.” He’s never been so grateful for the dumb cargo pockets on his track pants. He has a good feeling about Castiel. “Do you like cheeseburgers? I know a place that has the best burgers.”

“Oh my god.” Castiel walks over to one of the double benches in the gazebo and sits, looping Cordon’s leash around one of the carved legs. The dog lays down after a moment, flopping over happily as Castiel gazes up at Dean. “It might make me sound like a teenager, but I’m sure burgers are my favorite food. A good burger…” Castiel gets a longing look on his face before heaving a deep sigh. “Makes me very happy.” 

His phone is out and he waits with heavy expectation for the number Castiel is about to give him. They’re going to have an awesome first date, the food is going to blow his mind and Dean is going to take his time and pick apart all the other little things he wants to know. Taste in films and music, what Castiel does for a living, what he looks for in a partner, how he feels about family; one thing was checked off already, he likes dogs.

After Castiel gives him his number and Dean saves it, he fidgets on his feet for a moment before joining Castiel on the dog-bone shaped bench that he had donated to the park. This was one of the four he had made and it felt cosmically weird to sit down next to Cas and feel like something momentous was happening as he shifted his thigh closer to the other man.

Blue eyes flicked a look at him, as Dean tried to be all cool and casual as he let his hand rest palm up on the leg resting next to Castiels’. Their gazes met again, and it seemed like a moment suspended before Castiel looked away with a hoarse sound caught in his throat.

“This is going to sound so weird.” His left hand tracing the bench arm as Dean tries to mentally figure out if he’s just really fucking attracted to this dude or going out of his mind. He wants to hold the hand of a guy he met less than an hour ago, desperately, like he’s a six-year-old on the playground with a crush again. “But umm...I don’t-don’t just give my number to guys in the dog park! Or decide to go out with them, but I like what I’m feeling here and I…I feel good.”

“Gay?” Jokes are how he deals with discomfort and luckily Castiel doesn’t seem offended by his deflection, his smile still warm and small before he looks down at Dean’s hand.

“Yeah...happy.” And when he takes his hand determinedly, intertwining their fingers together Dean feels butterflies. 

He’s regressed to a teenager. He’s fucking grinning from ear to ear down at his lap like one. They both just revel in the warmth they feel from holding hands and stare away, that is until Castiel knocks his knuckles on the armrest he had been tracing delicately earlier.

“It’s even weirder that we’re sitting on the reason we met today.” That makes Dean blink and look back at Castiel with a perplexed look on his face.

“What?” When his electric blue eyes see Dean’s clear confusion, Castiel shakes his head and explains.

“I went to Park Services because I wanted to find out who made the benches, but all they could tell me was they were donated to the park last week, which I already knew. I come here every day, so I noticed the additions. They told me that these two are here and another two were taken to the other side of the city to another dog park.” The other park he takes Zepp to, Dean’s mind supplies with a slack jaw as he stares and Castiel keeps talking, eyes on their joined hands now. “Apparently they don’t know who made them, and if I want to find out who donated them, I’d have to go to the City Council and ugh.” Castiel’s shrug is felt through his arm, Dean squeezing back with his fingers though he’s still speechless because what are the goddamned odds.

“There’s a plaque, under the backbone on the seat. Just a little square with the artists’ initials.” Dean chokes it out, pointing over past Castiel at the break in the two planks. “Reach through there and feel right in the corner.”

Castiel tilts his head and squints at him, lips pursing. “Really?” But he does as Dean says and uses his free hand, twisting his body away from Dean’s. He sees Castiel’s face light up when he feels the initials on the plaque, a small smile on his lips as he looks back at Dean. “Hey! How did you know?”

Dean shrugs his grin in return, weak and self-conscious as he blushes. “Uh, I made them. It's a D.W. you’re feeling up right now.”

He watches Castiel’s eyes go wide and his jaw drops with a shy satisfaction and rubs the back of his neck bashfully as he stares back. “Hi. Glad you like my work?”

“You’re a woodworker?” Their knees knock together as Castiel twists to face him but he’s still holding his hand so... 

Dean ducks his head in a nod. “Yeah. I’ve got a line of furniture in distribution, and I make some tiny things for my shop, just for...you know, family and friends and,” Dean waves around his free hand. “My dog park.”

Cas' eyes are unbelievable, Dean decides as he catches himself just staring into Castiel’s barely blinking, too-blue eyes. The man just nods, sort of dazedly as he is the first to break their impromptu staring contest.

“Friday, seven. Wherever your burger place is.” Castiel says with a conviction that provides zero room for negotiating that Dean finds really freaking hot.

“Yeah, Friday.” 

Because how could he turn him down when the stars are finally aligning for once in his life.

**Notes for the Chapter:**

> Comments welcomed and kudos loved! <3

**Author's Note:**

> This new series of drabbles and ficlets is the _fault_ of my new friends on Discord The Profound Bond server <3
> 
> As usual, comments loved and kudos welcome!


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